When Jerry Jones bought the Dallas Cowboys in 1989, he had to be looking at some mirror making a monologue and promising big changes. His entire ownership with the Cowboys has been a lot of twists and turns in which no one knows what to expect from the corkiest owner in the NFL. Not only has he made the league as a whole much more financially stable because of his myriad of ideas, but he has also challenged players, other owners, and commissioners who stand in his path.
What can’t be taken away is the fact that Jerry Jones is a Hall of Famer in the NFL and owns a team that won three Super Bowls under his watch. That is something that many can’t say they’ve done and Jerry has to be very proud of those accomplishments. The Cowboys team in the '90s was completely stacked and looked like a new version of the NFL when they first burst onto the scene. The team that managed to win three Super Bowl rings in four years somehow quickly collapsed.
That is where we get to this list. Jerry Jones has all of that success, yet he has made some of the more questionable moves in NFL history. On one end Jerry is such a brilliant businessman, but his flaws as a talent evaluator have shown over the past 25 years without Jimmy Johnson. These strange moves will be discussed for a long time in NFL circles but one thing is clear: there will never be another Jerry Jones.
20 Signing Mike Vanderjagt
In 2006, kicker Mike Vanderjagt became a free agent. He was known for his great accuracy throughout the season. You knew beforehand that there was something actually on the line in one of those crucial moments. But in 2005, he hit an amazing 92 percent of his field goals.
The Cowboys decided they were going to gamble by signing the 36-year-old kicker to a three-year, $6 million deal.
Well, the results were an all-out disaster as Vanderjagt hit only 72 percent of his field goals throughout the season and only kicked in ten games for the team in 2006. After that Vanderjagt never played for the Cowboys again and they were on the hunt for another kicker.
19 Drafting Steve Walsh
In 1989, the Cowboys figured that they had their quarterback of the future when they took Troy Aikman with the first overall pick in the draft. Of course, going by the policy that you can never trust a sure thing the Cowboys took quarterback Steve Walsh with the first pick of the supplemental draft. This meant that they gave up a future first-rounder to take Walsh with this pick and would be losing their draft pick in 2010.
This move was bound for failure one way or another as Walsh was the QB who didn’t pan out. That being said, it was an interesting method of hedging your bets that hasn’t been tried since in the NFL.
18 Trading For Drew Henson
Drew Henson started off his professional sports career as a baseball player in 1998. Henson actually got into the majors and played for the Yankees for a little bit before ultimately failing to make an impact. Henson then decided that he would just waltz on over and give football a shot after not playing the sport for years. Still, because of his physical attributes, the Texans took Henson in the sixth round of the 2003 draft. While it’s an interesting move, that’s nothing that would stun anyone… until the Cowboys flipped a third-round pick in 2005 for Henson to play quarterback for the team in 2004. He played a grand total of one game for the Cowboys, and just like that, the Drew Henson experiment was over.
17 Signing Greg Hardy
Greg Hardy was one of the NFL's most dominating pass rushers for the Carolina Panthers. However, after he missed most of the 2014 season due to off-field issues, things had reached a point where no one wanted to touch Hardy in the offseason. That is, no one except Jerry Jones, as he didn’t read the room and took a chance on Hardy anyway.
He ended up with 6 sacks in one season with the team before being released in the offseason.
Considering the things that were happening off the field this was one of the worst decisions Jerry ever made, and Hardy hasn't played in the NFL since, having moved on to a mixed martial arts career.
16 Firing Jimmy Johnson
Signing Jimmy Johnson was one of the best moves that Jerry Jones ever made. With Johnson leading the team the Cowboys won the Super Bowl in 1992 and 1993 and looked posed to become maybe the biggest dynasty the NFL had ever seen. They were still young and with Johnson in control of the player personnel, they continued to draft very talented players and plug them into the system. But egos got in the way a little quicker than you would expect as Johnson and Jones started to clash heads before ultimately Jones took control of the franchise. Which led to…
15 Hiring Barry Switzer
How do you make any coaching change worse in the NFL? For a long time in the '90s, the answer was to hire Rich Kotite or Barry Switzer. Alas, only one person did the latter and that was Jerry Jones. With a system that was perfectly made to win at least three more Super Bowls, Switzer quickly made the high powered machine that was the Cowboys break down into a heap on the side of the road. They won a Super Bowl in 1995 with Switzer “leading” the charge but when 1997 rolled around, the Cowboys went 6-10 and Switzer was quickly out of the door. Jones just hired the wrong guy and that ended up crushing a dynasty which should have been even better.
14 Signing Terrell Owens
In fairness, I think this is one of those mistakes in which you can’t blame Jerry for trying. He had a team that he felt needs one more weapon on the outside and who else to get for a perfect two-year rental than TO? Given the context in 2005, the Cowboys went 9-7 and just missed the playoffs.
They truly thought they could explode with TO on the roster, and while 2006 was a disappointment, in 2007 there was a changing of the guard with Tony Romo starting at QB and Wade Phillips taking over as coach.
They won 13 games before losing their first game in the playoffs. But the ticking timebomb of TO finally went off, went he started blaming Romo for his passing decisions and caused another locker room schism as only he can.
13 Trading Draft Picks For Roy Williams (WR)
Roy Williams was seen as a very good receiver who could have a great year given certain circumstances. After he got 1,300 yards in 2006, Williams couldn’t repeat that performance and the Lions decided to move on from him. Luckily for them, Jerry Jones was around willing to trade away everything but the kitchen sink to get a wideout to play on the opposite side of Terrell Owens.
Jones traded future first, third, and sixth-round picks to the Lions for Williams. But it seemed like the second Williams became a Cowboy he was slow, stiff, and couldn’t run routes anymore. Williams ended up never reaching 600 yards with the team in three seasons.
12 Firing Tom Landry
This is a tough thing to put on this list for a few reasons. The first and most obvious one being that it was time for Tom Landry to go. He had been coaching the Cowboys since 1960 when 1988 rolled around. That means he was in the NFL for an astounding 29 years. But in the last three seasons of his tenure, Landry went 7-9, 7-8, and 3-13 to finish it off. The second thing is that Jimmy Johnson was absolutely the right pickup for the future of the team.
Each part of this move was perfect except the execution, which didn’t give Landry the dignity he deserved on his way out of the door after winning two Super Bowls with the Cowboys.
11 Signing Joey Galloway
This is another tough one to blame on Jerry because of certain things surrounding what actually happened around the move. Joey Galloway was considered the fastest wide receiver in the NFL when the Cowboys made the plunge to pick up the 29-year-old wideout in free agency. Now it’s easy to point out why this didn’t work.
At that age, receivers just run out of steam in the long term and get older.
Galloway never had 1,000 yards with the team so it checks out. Except when you look back and realize he had three 1,000 seasons with the Buccaneers, including one when he was 36 years old. It’s a little of both, but this one is more on the coaching staff than Jerry.
10 Drafting Shante Carver
For the most part, this move is the hallmark terrible Jerry Jones pick. It was 1994 and the first year without Jimmy Johnson running the show. That meant that Jerry finally could be in charge of everything and make the right moves to keep the Cowboys as the most talented team in the NFL. In fairness, there weren’t much better pass rushing options at that point in the draft, or a lot of players right around that pick that panned out in general. Still, when you draft a guy who only plays four seasons and only gets 11.5 sacks in his career, you must get called out for it.
9 Drafting Quincy Carter
Quincy Carter was supposed to be the future of the Cowboys at quarterback. They were tired of not having an established guy since Troy Aikman, so when Carter was picked in the second round in the 2001 draft, he was being prepared to take that role. Carter never stood a chance starting for the team and struggled mightily. He ended up starting 31 games for the team in three years and throwing 29 TDs to 36 INTs. Those were bad numbers which the Cowboys simply couldn’t stomach anymore, and in 2004, they decided to move on.
8 Drafting Roy Williams (FS)
Yes, the other Roy Williams also has a spot on this list. You would think that, as a pure karma thing, maybe Jerry Jones wouldn’t have traded for the wideout Williams simply because of what Williams the safety ended up looking like. To be fair, this Roy Williams was a solid player for the Cowboys and an enforcer in the middle of the field.
He wasn’t the best in coverage, but it didn’t matter, because the man could hit.
That being said with the eighth pick in the draft, you can’t just be a solid player; you have to be great. To make things worse, Ed Reed was picked 24th in that draft. It's rough when someone you pass on in the same position ends up becoming a Hall of Fame-caliber player, but that’s how it goes sometimes.
7 Signing Pacman Jones
This was a move that everyone thought was dumb from the beginning. Every person saw this and just decided that Jerry was trying to really be the rebel of the NFL. Cornerback Adam “Pacman” Jones was always in the commissioner’s office getting long suspensions. This was at a time when Roger Goodell was handing them out like hotcakes, but he was still the guy getting the brunt of it. The Cowboys went on and signed him regardless and Jones played 9 games for the team, recording no INTs.
What's unfortunate is the timing, because Jerry was right about the talent. Jones turned out to be a solid player for the Bengals for eight years. Back then, it just wasn’t the time to make that move, though.
6 Ezekiel Elliott's Suspension
We may never know what really happened with running back Ezekiel Elliott and his off-field issues last year. But it is completely understandable that Jerry would want to stand by his guys and not want anything negative on their record, at least in the court of public opinion. However, given how the season played out it was the wrong decision for Jerry to make. By doubling down, Zeke missed games later in the season which were more important, and led to the Cowboys missing the playoffs after going 13-3 in 2016. It was a tough decision to make, but Jerry should have stepped back and not tried to fight it as much with Zeke.
5 Allowing DeMarco Murray To Leave
This is one of the rare moves that Jerry Jones actually fixed himself and didn’t luck into an undrafted quarterback situation but look at how bad this decision was.
Running back DeMarco Murray ran for over 1,800 yards and 13 TDs as the Cowboys went 12-4 before falling in the playoffs.
Still, 2015 was supposed to be a year in which the Cowboys kept climbing to greatness, but it took a slight detour because the Cowboys decided that anyone with two legs could run for 1,300 yards behind their offensive line. In fairness, Darren McFadden did get 1,000 yards in 2015 and Jerry did luck into drafting Ezekiel Elliott because they were so bad that year. But he made a great choice and the Cowboys running game is back so it all worked out.
4 Drafting Morris Claiborne
The Cowboys were sitting pretty with the sixth overall pick in the loaded draft of 2012. This was the one which had RGIII and Andrew Luck, but there were a lot of other extremely talented players up and down this draft. However, Jerry took Morris Claiborne, a cornerback who only had five interceptions in five years, with the golden pick.
Defense was loaded in this draft and Jerry Jones managed to pass up on Fletcher Cox, Luke Kuechly, Melvin Ingram, Don’t’a Hightower, Chandler Jones, Whitney Mercilus, Bruce Irvin and secondary players Harrison Smith, Stephon Gilmore, and Dre Kirkpatrick. All of those players weren’t sleepers either; they were all picked in the first round of the draft, which is amazing. Yet somehow Jerry didn’t take any of them.
3 Letting DeMarcus Ware Walk
DeMarcus Ware was the only player on the Cowboys since 2000 who really put fear in the heads of offensive players. He was an incredible talent who got 117 sacks in 9 years with the team. That is a staggering amount and there were times when Ware was the best pass rusher in the NFL with 20 sacks in 2008. But he started slowing down over the years and they decided to let him walk. Ware went on to win a Super Bowl with the Broncos in 2015 while the Cowboys were close in 2014 but lost in the divisional round. Do they lose to the Packers in 2014 against a hurt Rodgers if Ware is there to track him down a few times? It’s tough to say but given his career and how he helped the Broncos, it’s safe to say Ware could have made a few impact plays in that game.
2 Jason Garrett As Coach
From the minute Jason Garrett was on the sidelines getting paid more money than Wade Phillips this was bound to happen. No, the ex-quarterback wasn’t on the sidelines in that quasi-backup role where you are also coaching, but on Phillips’ staff as an offensive coordinator.
Jerry definitely had some sort of connection with Garrett, because after Phillips got fired he was promoted to the head coaching position.
Garrett has gotten a much longer leash than Phillips ever dreamed of. In his eight seasons as head coach, Garrett has an average record and is 1-2 in the playoffs. Those aren't great numbers for the prodigal son.
1 Passed on Randy Moss
If you ever want to know if a move is bad, go watch the actual draft live. That is when you can see if the people watching are as surprised as you would have been watching the same move take place today. In live action people, were stunned that the Cowboys passed on Randy Moss with the eighth overall pick in the draft and instead took Greg Ellis.
To make things worse there is footage of the Cowboys war room in which a longtime scout Jim Garrett had this money quote: "Men, this is not the Boy Scouts we're dealing with. This is pro football. Draft him." It's a beautiful line and one that Jerry has listened to hundreds of times. But this was the 101st time. Instead, Moss ended up torching the Cowboys for the legendary 3 catches/163 yards/3 TD game on Thanksgiving, and they have never lived down that mistake.